(S)-1-[(tert-butoxy)carbonyl]-6-methyl-piperidin-2-one | 269066-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-1-[(tert-butoxy)carbonyl]-6-methyl-piperidin-2-one
• 英文别名: (2S)-2-methyl-N-tert-butoxycarbonylpiperidin-6-one；N-BOC-6(S)-methyl-piperid-2-one；tert-butyl (2S)-2-methyl-6-oxopiperidine-1-carboxylate
• CAS: 269066-57-1
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: YAGAVXVWDVQSSM-QMMMGPOBSA-N

物化性质

• 沸点：
  326.4±11.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-[(tert-butoxy)carbonyl]-6-methyl-piperidin-2-one 在 platinum(IV) oxide 正丁基锂 、 TEA 、 氢气 、 N,N-二异丙基乙胺 、 三氟乙酸 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 (3S,3aR,4R,4aS,8aR,9aS)-decahydro-3-methyl-4-[2-(E)-[(2R,6S)-6-methylpiperidin-2-yl]ethenyl]naphtho[2,3-c]furan-1(3H)-one
  参考文献：
  名称：

  （+）-半纤维素的仿生全合成。

  摘要：

  在用三氟乙酸处理时，丁烯内酯14进行N-Boc脱保护和缩合，然后进行亚胺离子活化的分子内Diels-Alder环加成反应，从而在还原反应中得到（+）-半胱氨酸前体11。在四个合成步骤中将化合物11转化为（+）-半胱氨酸。[反应：看文字]

  DOI：

  10.1021/ol047676+
• 作为产物：
  描述：

  Boc-L-beta-高丙氨酸 在 platinum(IV) oxide 4-二甲氨基吡啶 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 (S)-1-[(tert-butoxy)carbonyl]-6-methyl-piperidin-2-one
  参考文献：
  名称：

  Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor

  摘要：

  tert-Butyl 2-substituted 4,6-dioxo-1-piperidinecarboxylates 4 have been prepared in good yield starting from Boc-Asp-(OBu)-Bu-t and other beta-amino acids. By analogy with chiral tetramic acids, their reduction by NaBH4 in CH2Cl2/AcOH afforded the corresponding cis-4-hydroxy delta-lactams in good yield and stereoselectivity (68-98% de). In the absence of the A(1,3) strain (reduction of 6-substituted 2,4-dioxo-1-piperidines 7), the cis-4-hydroxy isomer was still obtained as the major product but the de values were consistently lower. 4-Hydroxy-6-oxo-1,2-piperidinedicarboxylate 2a, readily accessible from Boc-Asp-OtBu (three steps, 63% overall yield), has proven to be an excellent building block for the synthesis of cis- and trans-4-hydroxypipecolates 17 and 24 (52 and 36% overall yield, respectively) and for the synthesis of a protected 4-hydroxylysine derivative 29 (41% overall yield).

  DOI：

  10.1021/jo0353886

文献信息

• [EN] NICOTINIC RECEPTOR TARGETED COMPOUNDS AND COMPOSITIONS<br/>[FR] COMPOSÉS ET COMPOSITIONS CIBLANT UN RÉCEPTEUR NICOTINIQUE
  申请人：UNIV FLORIDA

  公开号：WO2013090260A1

  公开（公告）日：2013-06-20

  The invention relates to the design and synthesis of novel anabaseine-based compounds, which are useful in treating or preventing a wide variety of conditions, including nervous system diseases or disorders, such as, schizophrenia, Alzheimer's disease, Parkinson's disease, drug dependence, and substance addiction, and compositions, kits, and methods thereof. The invention also provides novel anabaseine-based compounds, compositions, kits, and methods thereof for treating or preventing non-nerve system diseases or disorders (such as, inflammation and cancer) in a subject identified in need thereof. Certain enantiomeric compounds of the invention exhibited enhanced selectivity toward α7 nAChRs relative to alpha4beta2 nAChRs. Other enantiomeric compounds of the invention exhibited enhanced selectivity for alpha4beta2 nAChRs relative to α7 nAChRs.

  该发明涉及设计和合成新型基于阿那巴胆碱的化合物，这些化合物在治疗或预防多种疾病条件中非常有用，包括神经系统疾病或障碍，如精神分裂症、阿尔茨海默病、帕金森病、药物依赖和物质成瘾，以及相关的组合物、试剂盒和方法。该发明还提供了用于治疗或预防非神经系统疾病或障碍（如炎症和癌症）的新型基于阿那巴胆碱的化合物、组合物、试剂盒和方法，用于满足需要的受试者。该发明的某些对映体化合物表现出相对于α4β2 nAChRs的增强选择性，而其他对映体化合物表现出相对于α7 nAChRs的增强选择性。
• Nicotine receptor targeted compounds and compositions
  申请人：University of Florida Research Foundation

  公开号：US09150558B2

  公开（公告）日：2015-10-06

  The invention relates to the design and synthesis of novel anabaseine-based compounds, which are useful in treating or preventing a wide variety of conditions, including nervous system diseases or disorders, such as, schizophrenia, Alzheimer's disease, Parkinson's disease, drug dependence, and substance addiction, and compositions, kits, and methods thereof. The invention also provides novel anabaseine-based compounds, compositions, kits, and methods thereof for treating or preventing non-nerve system diseases or disorders (such as, inflammation and cancer) in a subject identified in need thereof. Certain enantiomeric compounds of the invention exhibited enhanced selectivity toward α7 nAChRs relative to alpha4beta2 nAChRs. Other enantiomeric compounds of the invention exhibited enhanced selectivity for alpha4beta2 nAChRs relative to α7 nAChRs.

  本发明涉及设计和合成新型基于阿那巴烟的化合物，这些化合物可用于治疗或预防各种疾病，包括神经系统疾病或障碍，如精神分裂症、阿尔茨海默病、帕金森病、药物依赖和物质成瘾，以及其组合物、试剂盒和方法。本发明还提供了新型基于阿那巴烟的化合物、组合物、试剂盒和方法，用于治疗或预防非神经系统疾病或障碍（如炎症和癌症）的需要识别的受试者。本发明的某些对映体化合物表现出相对于α4beta2 nAChRs增强的α7 nAChRs选择性。本发明的其他对映体化合物表现出相对于α7 nAChRs增强的α4beta2 nAChRs选择性。
• RETRACTED: Biomimetic approach to Galbulimina type I alkaloids
  作者：Kirill Tchabanenko、Richard Chesworth、Jeremy S. Parker、Neel K. Anand、Andrew T. Russell、Robert M. Adlington、Jack E. Baldwin

  DOI：10.1016/j.tet.2005.09.050

  日期：2005.12

  On treatment with trifluoroacetic acid the tetraene precursor 23 underwent Boc deprotection, condensation and an iminium ion accelerated intramolecular Diels-Alder cycloaddition resulting in an iminium species 12, which was further converted into himbacine 1, himbeline 3 and himandravine 4, three out of four Galbulimina type I alkaloids thus providing strong evidence for the proposed biogenesis of this important family of alkaloids. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereoselective Alkylation of <i>N</i>-Boc-protected-5-substituted δ-Lactams:  Synthesis of <i>α</i>,δ-Disubstituted δ-Amino Acids
  作者：J. Richard Casimir、Claude Didierjean、André Aubry、Marc Rodriguez、Jean-Paul Briand、Gilles Guichard

  DOI：10.1021/ol9913136

  日期：2000.4.1

  [GRAPHICS]N-Boc-protected-5-substituted delta-lactams were readily prepared from the corresponding beta(3)-amino acids. Alkylation reactions of their Na enolates with various electrophiles proceeded in high yields with high facial selectivity. The structure of the alkylation products was confirmed by Single-crystal X-ray analysis. This method provides a fast access to optically active alpha,delta-disubstituted delta-amino acids.
• US20140343042A1
  申请人：——

  公开号：——

  公开（公告）日：——